Cyclohexyl resorcin and process of making the same



Patented Nov. 22, 1927.

4 UNITED STATES MAX PHILLIPS, F EVANSVILLE, WISCONSIN.

CYCLOHEXYL RESORGIN AND PROCESS OF MAKING THE SAME.

No Drawing.

The invention relates to the preparation of a new derivative of resorcin having useful medicinal properties.

It is already known that alkyl derivatives Application filed A ril as,

1926. Serial No. 105,264.

\Vhereas -in the above example cyclohexa- 1101 was condensed with resorcin, other de-' rivatives of cyclohexane,-such as chlor, brom or iodocyclohexane, may-be used in place of 5 of resorcin have germicidal properties, the the. cyclohexanol. When the halogen derivgermicidal efiect increasing with the size of the alkyl group and reaching a maximum with the normal six carbon chain or the N. hexyl group. A normal hexyl derivative of resorcin under the .name hexyl resorcin or Caprokol has found wide;use, particularly as a urinary antiseptic. The chief objection to the hexyl resorcin from a chemical standpoint is that one of the raw materials, namcvorably with the published data on hexylresorcin, and has the further advantage that the raw materials, namely, cyclohexanol and resorcin are cheap and readily obtainable. The cyclohexanol is obtained commercially by the catalytic'hydrogenation of phenol.

.An example of the manner in which I proceed with the preparation of, cyclohexyl resorcin is the following". without limiting myself as to any particular temperature or condensing agent:

Ten pts. cyclohexanol, 22 pts. resorcin and I 3.5 pts. anhyd. ZnCl are placed in'a suitable vessel and heated until-the reaction begins,

which is approximately 150 C. Heating is continued until there is no further reaction.

The reaction product is thoroughly washed with H O and product distilled under reduced pressure, The fraction boiling 165- 185 C. at 2 mm. pressure is retained. --This is a nearlycolorless liquid which solidifies at room temperature, and when crystallized from a suitable solvent, such as benzol or a mixture of benzol and petroleum ether, the

- cyclohexyl resorcin is obtained as colorless plates melting at 124 C. (corrected).

H 80 anhyd. FeCl etc.,' may be used in,-

stead, although I prefer to use anhyd. ZnCI The term derivative of cyclohexane as used'in the specification and the claims is intended to include in its definition substitu tion products of cycloliexane, where one or more hydrogen atoms have been replaced by chlorine, bromine, iodine, hydroxyl', alkoxyl,

alkyl, aryl and aryl-alkyl group or groups.

Having now described my invention, What I claim and desire to have protected by Letters Patent is:

1. new chemical compound, cyclohexylresorcin. I

2. A process of making cyclohexyl-resorcin consisting in the condensation of a negative substituted cyclohexane and resorcin. 3. A process of makin cyclohexyl-resorcin consisting in the con ensation of cyclohexanol and resorcin. H

4. Aprocess of making cyclohexyl-resor: cin consisting in the condensation of a negative substituted cyclohexa'ne and resorcin tive substituted cyclohexane and resorcin 1n the presence of anhyd. zinc chloride.

7. A process of making cyclohexyl resorcin consisting in the condensation of cyclohexanol and resorcin in thepresence of anhyd. zinc chloride.

MAX PHILLIPS. 

